The invention relates to a plasticizer, which can be used in coverstocks for bowling balls.
Polyurethane raw materials have been used for bowling ball coverstocks for many years. Polyurethanes are used industry-wide for professional bowling balls (and high-end amateur products) because they provide the necessary on-lane performance required at this high level of play.
In the game of bowling, a skillful bowler generally rolls the ball down the bowling lane such that the bowling ball enters the pin placement at an angle with respect to longitudinal axis of the bowling ball. It is generally known that the larger the angle the bowling ball travels before it hits the pins, the larger the area of impact with the pins, thereby resulting in more pins being knocked down or if all ten pins are knocked down, a xe2x80x9cstrikexe2x80x9d is thrown.
Therefore, of particular importance is the ability of the ball to xe2x80x9chookxe2x80x9d near the end of the bowling lane when thrown with spin. The bowling community calls this hooking performance xe2x80x9creactivityxe2x80x9d and a ball that hooks well is known as a xe2x80x9creactive ball.xe2x80x9d
One of the most important formulation ingredients contributing to ball reactivity is the plasticizer. Plasticizers such as 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (Kodaflex xe2x80x9cTXIBxe2x80x9d), from Eastman Chemical Company, are used in polyurethane formulations for application as coverstocks.
An object of the present invention is to provide a bowling ball which is less sensitive to the effects of the oil on a bowling lane. The plasticizers of the present invention achieve this result.
There is still, therefore, a need to create a bowling ball with better ball performance than the bowling balls having the conventional coverstocks.
Accordingly, the present invention provides plasticizer compounds represented by the formula: 
in which n=1 to 3, R represents a C2-C8 straight or branched aliphatic hydrocarbon chain or C6-C10 aromatic or cycloaliphatic group, and Rxe2x80x2 and Rxe2x80x3 are each independently a branched oxyalkylene chain represented by the chemical formula C8H16O and by the chemical structures: 
The present invention is also directed to a coverstock formulation comprising the plasticizer compound (1).
The present invention relates to a plasticizer compound having the general formula: 
in which n=1 to 3, R represents a C2-C8 straight or branched aliphatic hydrocarbon chain or C6-C10 aromatic or cycloaliphatic group, and Rxe2x80x2 and Rxe2x80x3 are each, independently, groups represented by the chemical formula C8H16O and by the chemical structures: 
R is understood to mean C2-C8 alkylene chains, C6-C10 cycloalkylene chains or C6-C10 arylene chains. In the case that R represents a C2-C8 alkylene chain, C2-C8 alkylenes are to be understood to mean all linear or branched alkylene residues with 2 to 8 carbon atoms, such as, ethylene, n-propylene, i-propylene, n-butylene, i-butylene, n-pentylene, i-pentylene, neopentylene and hexylene, which, in turn, may again be substituted. By way of substituents in this connection, halogen, or C2-C8 alkyl or alkoxy, as well as C6-C10 cycloalkyl or C6-C10 aryl, come into consideration, such as chloroethylene, cyclohexylethylene or phenylethylene.
In the case that R represents a C6-C10 cycloalkylene chain, C6-C10 cycloalkylene is to be understood to mean all mononuclear or polynuclear cycloalkylene residues with 6 to 10 carbon atoms, such as cyclohexylene, cycloheptylene, which, in turn, may again be substituted. By way of substituents in this connection, halogen or also C2-C8 alkyl or alkoxyl, as well as C6-C10 cycloalkyl or C6-C10 aryl, come into consideration. C6-C10 cycloalkylene can also include structures with fatty hydrocarbon chains pendant from a cycloaliphatic ring, such as products derived from the materials collectively referred to as xe2x80x9cdimer acidsxe2x80x9d. In this. case, even though the total structural fragment separating the ester carbonyl groups is greater that C6-C10 (typically around C36), the chain directly connecting the carbonyl groups is still in the range of C6-C10.
C6-C10 arylene is to be understood to mean all mononuclear or polynuclear aryl residues with 6 to 10 carbon atoms, such as phenylene or naphthylene, which, in turn, may again be substituted. By way of substituents in this connection, halogen, or also C2-C8 alkyl or alkoxyl, as well as C6-C10 cycloalkyl or C6-C10 aryl, come into consideration.
Preferred embodiments of the present invention include examples in which R represents an octamethylene chain, a tetramethylene chain or a 1,2-phenylene group.
Examples of plasticizer compounds of the present invention include di-Texanol sebacate, and di-Texanol adipate and di-Texanol phthalate having. the following simplified structures, respectively: 
During the preparation of the plasticizer compounds of the present invention from one mole of dicarboxylic acid and two moles of the mono-hydroxy compound xe2x80x9cTexanol,xe2x80x9d which is a registered trademark of Eastman Chemical Company, (2,2,4-trimethyl-1,3-pentanediol monoisobutyrate), the major product is the 2:1 adduct represented by the structure with n=1. However, small amounts of the product corresponding to the structure with n=2 or n=3 may be present from reaction of the carboxylic acid reactant with traces of 2,2,4-trimethyl-1,3-pentanediol in the 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, or from transesterification of one of the isobutyrate groups. Further, since the monoisobutyrate material used for preparation of the plasticizer products contains a mixture of isomers, the plasticizer compounds of the invention also includes an isomeric mixture. Small amounts of 2,2,4-trimethyl-1,3-pentanediol diisobutyrate may also be present as a trace contaminant.
The plasticizer compound of the present invention can also be used as a plasticizer for PVC, as an additive for coatings or as part of wood preserving formulations. Such plasticizers may also be used as plasticizers in normal (soft) polyurethane elastomers. Most preferably, the plasticizer compound is used in a bowling ball coverstock to make a bowling ball.
The bowling ball coverstock of the present invention comprises at least one isocyanate, at least one active hydrogen-containing compound and various additives including the above-mentioned plasticizer compound of the present invention.
As isocyanates, those that are used, are aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic polyisocyanates, such as those described, for example, by W. Siefken in Justus Liebigs Annalen der Chemie, 562, pp. 75-136, for example, those of the formula
Q(NCO)n
in which n denotes 2-4, preferably 2-3, and
Q denotes an aliphatic hydrocarbon radical of 2-18, preferably 6-10 carbon atoms, a cycloaliphatic hydrocarbon radical of 4-15, preferably 5-10 carbon atoms, an aromatic hydrocarbon radical of 6-15, preferably 6-13 carbon atoms or an araliphatic hydrocarbon radical of 8-15, preferably 8-13 carbon atoms, for example, such polyisocyanates as described in DE-OS 2,832,253, pp 10-11.
Particularly preferred are usually those polyisocyanates which are technically readily accessible, for example, the 2,4- and 2,6-toluylene diisocyanate as well as any mixture of these isomers (xe2x80x9cTDIxe2x80x9d); polyphenyl-polymethylenepolyisocyanates, such as those obtained by an aniline-formaldehyde condensation and subsequent treatment with phosgene (xe2x80x9ccrude MDIxe2x80x9d), and polyisocyanates comprising carbodiimide groups, urethane groups, allophanate groups, isocyanurate groups, urea groups or biuret groups (xe2x80x9cmodified polyisocyanatesxe2x80x9d), especially those modified polyisocyanates which are derived from 2,4- and/or 2,6-toluylene diisocyanate and from 4,4xe2x80x2- and/or 2,4xe2x80x2- diphenylmethane diisocyanate. In a particularly preferred embodiment, a 131 equivalent weight polymeric isocyanate mixture having about 50% monomeric 4,4xe2x80x2-MDI, about 3% monomeric 2,4xe2x80x2- and 2,2xe2x80x2-MDI isomers and about 57% higher molecular weight homologues of the MDI series is desired.
The starting components may further be compounds of a molecular weight usually of 400 to 10,000, containing at least two hydrogen atoms reactive toward isocyanates. These comprise, besides .compounds containing amino, thio, or carboxyl groups, preferably compounds containing hydroxyl groups, in particular compounds containing 2 to 8 hydroxyl groups, especially those of a molecular weight of 400-8000, preferably 600 to 4000, for example, polyethers and polyesters as well as polycarbonates and polyester amides containing at least 2, usually 2 to 8, preferably 2 to 6 hydroxyl groups; these compounds are known per se for the preparation of homogenous and cellular polyurethanes and are disclosed, for example in DE-OS 2,832,253, pp. 11-18.
When appropriate, compounds comprising at least two hydrogen atoms reactive toward isocyanates and of a molecular weight of 32 to 399 may be used as further starting components. Also, in this case, compounds containing hydroxyl groups and/or amino groups and/or thiol groups and/or carboxyl groups, preferably compounds containing hydroxyl groups and/or amino groups, are understood to be those which are used as chain extenders or crosslinking agents. These compounds usually have 2 to 8, preferably 2 to 4 hydrogen atoms reactive toward isocyanates. Appropriate examples are disclosed in DE-OS 2,832,253, pp. 19-20.
Other compounds known to be useful in polyurethane formulations can also be used, including catalysts, surfactants, viscosity modifiers, stabilizers, release agents, drying agents, fillers and reinforcements.